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Peyote alkaloids: identification in a prehistoric specimen of lophophora from coahuila, Mexico Abstract Mescaline, anhalonine, lophophorine, pellotine, and anhalonidine have been identified in alkaloid extracts of a prehistoric specimen of Lophophora from a burial cave in west central Coahuila, Mexico. The specimen is associated with radiocarbon dates of A.D. 810 to 1070 and is one of the oldest materials ever submitted to alkaloid analysis. http://www.ncbi.nlm.nih.gov/pubmed/17796678
Prehistoric peyote use: alkaloid analysis and radiocarbon dating of archaeological specimens of Lophophora from Texas. Abstract Two archaeological specimens of peyote buttons, i.e. dried tops of the cactus Lophophora williamsii (Lem.) Coulter, from the collection of the Witte Museum in San Antonio, was subjected to radiocarbon dating and alkaloid analysis. The samples were presumably found in Shumla Cave No. 5 on the Rio Grande, Texas. Radiocarbon dating shows that the calibrated 14C age of the weighted mean of the two individual dated samples corresponds to the calendric time interval 3780-3660 BC (one sigma significance). Alkaloid extraction yielded approximately 2% of alkaloids. Analysis with thin-layer chromatography (TLC) and gas chromatography-mass spectrometry (GC-MS) led to the identification of mescaline in both samples. No other peyote alkaloids could be identified. The two peyote samples appear to be the oldest plant drug ever to yield a major bioactive compound upon chemical analysis. The identification of mescaline strengthens the evidence that native North Americans recognized the psychotropic properties of peyote as long as 5700 years ago. PMID: 15990261 [PubMed - indexed for MEDLINE] http://www.ncbi.nlm.nih.gov/pubmed/15990261
The shumla cave, Texas, lophophora williamsii buttons dating from 3780-3660 BC only contained mescaline, while the Coahuila, Mexico cave discovery dating from A.D. 810 to 1070 contained the full spectrum of peyote alkaloids. Amazing... Here's some comparisons to put this into perspective: There was a 2,700 year old grave of a gushi shaman found in the Gobi desert that contained around two pounds of cannabis that was determined to have been psychoactive, however all the active cannabinoids had long degraded http://www.nbcnews.com/i...na-stash-totally-busted/Regarding analysis of a near ancient banisteriopsis caapi vine, was this excerpt from the harmaline section of TIHKAL by shulgin: Quote:I was led to a comment that had been once made by a quiet hero of mine, Bo Holmstedt in Sweden, concerning the analysis of an ancient sample of plant material from Banisteria caapi (now known as Banisteriopsis caapi). The herbarium specimens he was looking at had been collected by the 19th century plant explorer Richard Spruce in the Rio Negro area of South America and had, after a few years of storage in a moist and mildewy hut a few miles down river, been rediscovered and sent on to the Kew Botanical Museum where they had quietly rested for over a hundred years. When Holmstedt worked them up some 30 years ago, he reported that the alkaloid content was 0.4%. This was virtually identical to a newly collected, botanically verified specimen of Banisteriopsis caapi which he analyzed at the same time and found to contain 0.5% alkaloids. The latter material contained, as described by many authors, the main alkaloids harmine, harmaline and tetrahydroharmine. By contrast, the alkaloid content of the Spruce material consisted exclusively of harmine. It is open to question whether the samples collected by Spruce in 1853 originally contained only harmine or, perhaps more likely, that harmaline and tetrahydroharmine have with time been transformed into the chemically more stable aromatic b-carboline harmine. -Tihkal;shulgin Still, none of these can compare to the ancient lophophora williamsii buttons which were discovered, the shumla cave loph. Buttons still contained 2% mescaline, and the loph. Buttons from Mexico still contained a full spectrum of phenethylamine alkaloids! -eg
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DMT-Nexus member
Posts: 876 Joined: 20-Apr-2012 Last visit: 12-Feb-2019
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Imagine if you had the chance to consume buttons that were that old (assuming they were OK to eat and not all moldy and decayed). Imagine the wisdom that is held within those, and the stories that they could show you. Everything published by Gone-and-Back are the mad rantings and ravings of a mind who yearns to be free and thinks he knows what he is talking about. However, these are just delusions made to feel that freedom, because that freedom will never come. Any experiments done are purely figments of the imagination, and are falsified to the highest degree. Nothing should be taken seriously from a crazy mans mind.
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DMT-Nexus member
Posts: 2889 Joined: 31-Oct-2014 Last visit: 03-Nov-2018
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Gone-and-Back wrote:Imagine if you had the chance to consume buttons that were that old (assuming they were OK to eat and not all moldy and decayed). Imagine the wisdom that is held within those, and the stories that they could show you. These were my thoughts as well, imagine consuming 5000 year old buttons (if they were even edible)... Even more fascinating is that after 5000 years, mescaline was still present...(The buttons from Mexico were less old, but contained the full spectrum of phenethylamine alkaloids. ) I attached a picture of ancient peyote ( peyote buttons recovered from a rock shelter in the lower Pecos River region (photo reproduced from Boyd et al. ) ) -eg entheogenic-gnosis attached the following image(s):  ancient_peyote_buttons.jpg (17kb) downloaded 160 time(s).
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DMT-Nexus member
 
Posts: 372 Joined: 29-Sep-2009 Last visit: 15-Feb-2024 Location: Diagonally parked in a parallel universe
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Strictly speaking those 5000 year old "buttons" weren't buttons at all. Martin Terry describes tham as effigies that were actually processed plant material made into the shape of peyote buttons. It is thought that the presence of only mescaline represents an ability of whoever made them to separate out the other alkaloids. I already asked Alice.
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DMT-Nexus member
Posts: 372 Joined: 29-Sep-2009 Last visit: 15-Feb-2024 Location: Diagonally parked in a parallel universe
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Deleted double post..  I already asked Alice.
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DMT-Nexus member
Posts: 876 Joined: 20-Apr-2012 Last visit: 12-Feb-2019
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pinkoyd wrote:Strictly speaking those 5000 year old "buttons" weren't buttons at all. Martin Terry describes tham as effigies that were actually processed plant material made into the shape of peyote buttons. It is thought that the presence of only mescaline represents an ability of whoever made them to separate out the other alkaloids. This is an interesting theory, but with them being that old I don't think this would be the case. It's more likely that mescaline is just that much more stable then the rest of the alkaloids that are present. Everything published by Gone-and-Back are the mad rantings and ravings of a mind who yearns to be free and thinks he knows what he is talking about. However, these are just delusions made to feel that freedom, because that freedom will never come. Any experiments done are purely figments of the imagination, and are falsified to the highest degree. Nothing should be taken seriously from a crazy mans mind.
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DMT-Nexus member
Posts: 2889 Joined: 31-Oct-2014 Last visit: 03-Nov-2018
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pinkoyd wrote:Strictly speaking those 5000 year old "buttons" weren't buttons at all. Martin Terry describes tham as effigies that were actually processed plant material made into the shape of peyote buttons. It is thought that the presence of only mescaline represents an ability of whoever made them to separate out the other alkaloids. http://www.ncbi.nlm.nih.gov/pubmed/15990261Chemical Analysis of lophophora williamsii; Radiocarbon dating puts them at 3780-3660 BC...which is around 5000 years old. Quote:Two archaeological specimens of peyote buttons, i.e. dried tops of the cactus Lophophora williamsii (Lem.) Coulter, from the collection of the Witte Museum in San Antonio, was subjected to radiocarbon dating and alkaloid analysis. The samples were presumably found in Shumla Cave No. 5 on the Rio Grande, Texas. Radiocarbon dating shows that the calibrated 14C age of the weighted mean of the two individual dated samples corresponds to the calendric time interval 3780-3660 BC (one sigma significance). Alkaloid extraction yielded approximately 2% of alkaloids. Analysis with thin-layer chromatography (TLC) and gas chromatography-mass spectrometry (GC-MS) led to the identification of mescaline in both samples. No other peyote alkaloids could be identified. The two peyote samples appear to be the oldest plant drug ever to yield a major bioactive compound upon chemical analysis. The identification of mescaline strengthens the evidence that native North Americans recognized the psychotropic properties of peyote as long as 5700 years ago. PMID: 15990261 [PubMed - indexed for MEDLINE] http://www.ncbi.nlm.nih.gov/pubmed/15990261 There were ceramic peyote representations discovered, however these are definantly not what I am referring to. I was speaking of the shumla cave Texas, and Mexico ancient peyote discovered and analyzed... I just could only find a picture from another case... (The picture was not of the ceramic representations, but that case was discussed when I was searching for a picture of the Mexican or shumla cave peyote. -eg
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DMT-Nexus member
Posts: 2889 Joined: 31-Oct-2014 Last visit: 03-Nov-2018
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Oh, damn... Ok, so your claim is that they were in fact "mashed up" peyote matter that was then compressed and shaped into representations of buttons... And the fact that only mescaline was present seems to suggest to you that these people had extraction techniques... I think I got it now.... Sorry for the misunderstanding.... Ha, I once consumed Macromerine pills that were pressed to look like peyote buttons...it's funny to think that 5000 years ago some people could have been experimenting with extracting similar compounds and pressing them into peyote representation pills... This was all regarding the shumla cave, Texas samples... It's funny that the Coahuila, Mexico ancient peyote samples still contained the full range of alkaloids... https://www.anoniem.org/....nih.gov/pubmed/17796678Interesting... My guess would be that 3,4,5-trimethoxy-phenethylamine is simply more stable over time than the Isoquinoline alkaloids such as anhalonine, lophophorine, pellotine, and anhalonidine... However I am very interested in your thoughts here... -eg
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Posts: 2889 Joined: 31-Oct-2014 Last visit: 03-Nov-2018
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Some discussion on the matter... Quote:One of these was from Cuatro Ciénegas, Coahuila, Mexico. This is a burial site from the transition between the Late Archaic and the Late Prehistoric Periods. The account of Bruhn et al. 1978 gave its age based not on the actual dating of the peyote but on the dating of material thought to be associated with that single set of 8 strung and remarkably well preserved peyote buttons. Three mats had been dated with a range of 810-1070 AD (uncorrected values). Due to the burial being a secondary interment, Martin Terry dated one of the actual Cuatro Ciénegas’ peyote specimens establishing its age as 835 ± 35 14C years BP. Shumla Cave (No. 5, 41VV113) in southwest Texas on the other hand was an inhabited residential site (with intrusion of several burials.) The peyote was believed to have been deposited in the Eagle Nest subperiod of the Middle Archaic Period. The exact provenience of the materials removed from the caves was not recorded but it is clear that they did mention recovering “a single mummified example” from Shumla Cave No. 5. This later became mistakenly presented as “petrified”. There was clearly more than one such artifact recovered from those excavations as three remained at the Witte for the removal of samples following the consumption of several others for earlier radiocarbon analysis. Terry et al. 2006 also reported their dating of the Shumla Caves’ peyote to 5195 ± 20 14C years BP. Summary of earlier dating accounts: Peter Furst was the first to report a date of 7000 BP for the Shumla cave material but due to several reasons the actual test data is either lost or irretrievable. It is therefore not possible to know anything further about the work or the claim. That claim oddly only appeared as a passing mention within a book review written by Furst. His date was repeated by Schultes & Hofmann and now appears stated as a fact throughout the literature. Bruhn et al. 2002 presented a letter to the editor of Lancet in which they asserted establishing peyote use for 5700 years after dating the Shumla material (Furst’s 7000 BP). They repeated the claims in DeSmet & Bruhn 2003 citing Bruhn et al. 2002 as their primary reference. El-Seedi et al. 2005 reported dating the Shumla Caves’ material to 3780-3660 BC. Jan Bruhn (in a personal communication with Martin Terry) reported this was a weighted mean of 4952 ± 44 14C years. Further investigation by Terry suggests that the discrepancy was most likely due to a failure of Bruhn to remove residual humic acid prior to radiocarbon dating. http://troutsnotes.com/archaic/ Quote:A fascinating analysis was performed, by Bruhn & workers, on the aforementioned specimen of Cuatro Ciénegas peyote (the string of buttons) which was found by Taylor in 1941.
Bruhn et al. 1978 found 2.25% alkaloid in the Cuatro Ciénegas’ material in spite of it being thought to be from around 810 to 1070 AD. Their analysis was reported to show it to contain mescaline, lophophorine, anhalonine, pellotine and anhalonidine present in measurable amounts.
Phenolic alkaloids formed 35% of the total. It was noted that this is substantially lower than the 8% total alkaloid and 64% phenolic fraction which they observed in recently prepared peyote buttons.
They used tlc and GC (both with known reference samples) to determine this. See Bruhn et al. 1978 for more details.
A peculiar assessment was more recently presented by Bruhn et al. 2002, also DeSmet & Bruhn 2003 and also El-Seedi et al. 2005 where it was being noted that the total alkaloid content was lower in the far older Witte material from the Shumla Caves. They then went on to assert that while only 2% alkaloid was present there was no alkaloid other than mescaline that was detectable. That was intriguing enough but was not the end.
Bruhn then made the peculiar proposal that the reason they could only detect mescaline could be due to mescaline being more stable than the other peyote alkaloids. Reasonable enough on the surface yet it is noteworthy that in this Bruhn failed to mention any of his own previous work that contradicts this claim. Clearly something is in need of closer inspection. This claim about the Shumla specimens needs consideration in the light of his 1978 Cuatro Cienegas results. There was also his earlier report concerning degradation of peyote alkaloids in the study of 87 year old peyote buttons in Bruhn & Holmstedt 1974. In particular, their determination clearly showing that mescaline content apparently decreased *ahead* of the rate of decomposition of many of the other alkaloids. The cherry-picked selective presentation of facts in their 2002/2003/2005 account appear to have been overlooked by Bruhn’s peer reviewers or at least they dropped the ball in terms of what peer review is meant to accomplish. That is all actually fairly however when trivial compared to what they AND Bruhn’s crew missed.
The most interesting aspect of this so-called ‘mummified’ material in my mind is that, unlike Bruhn, Furst or Taylor, Terry & coworkers recognized that the specimens were not dried peyote buttons at all but rather were manufactured effigies of peyote created from some type of doughy material. -eg
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Posts: 2889 Joined: 31-Oct-2014 Last visit: 03-Nov-2018
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Quote:One thing that is clear, these ‘buttons’ were clearly manufactured artifacts. To be able to retain 2% mescaline after 5 millennia would require it to have once have had a far higher alkaloid content. The presence of ONLY mescaline would not be a result of some magical selective degradation process omitting mescaline but would absolutely require the involvement of some type of purification process. Or perhaps there are missing elements of this tantalizing puzzle that are presently defeating our understanding of exactly what has been established in these studies.
Did these prehistoric people really know of a route for purifying or at least greatly concentrating mescaline? It would certainly be interesting if true but establishing that Bruhn’s analytical results were actually valid has to be the starting point for answering this peculiar question and the burden of proof for establishing their validity is on the authors of that work.
Were these potent effigies a prepared drug form that were created for sacramental use rather than for simple use as effigies? No matter how they were prepared and no matter what their alkaloid content, they are clearly both deliberate and sophisticated in their preparation.
Or are Bruhn/El-Seedi/DeSmet’s reported analytical results simply needing to be questioned?http://troutsnotes.com/archaic/ Keeper trout does raise some good points here... I need to further investigate all this... -eg
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http://troutsnotes.com/archaic/The quoted section in the above post was sourced from the above link. -eg
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A couple of striking factors exist concerning those peyote effigies from Shumla.
One is what was mentioned above, they were clearly manufactured items as their internal composition resembles 'chipboard' and are, with certainty, not botanical specimens, which is mind boggling considering they represent the oldest known 'peyotes'.
The other is there were two different formulas used between the three artifacts with two of them containing fibrous material from a noncactaceous (C3 rather than CAM) plant and one being from CAM plant tissues (Terry suggested it possibly might have used Opuntia tissue as the binder rather than something like sage). C3 and CAM plants are differentiable by their -𝛅13C values.
The details in Bruhn's other work in this area (in Bruhn et al 1978 and in Bruhn and Holmstedt 1974) indicated that mescaline is not actually more stable than many of the other peyote alkaloids so El-Seedi's more recent speculation that might explain the purported 2% needs some support.
A point raised in the thread above reveals a confounding factor as to why no more is known and most likely will never be known. A surprising number of peyotes have been reported to have been recovered in archaeological digs in that part of Texas (and one in New Mexico). Almost all are now unlocatable and are missing from the museums recieving them. The majority of those valuable historic specimens have been lost and cynical observers suspect that they were probably stolen and eaten by grad students with access although it is plausible something may still exist in someone's private 'collection'.
There is apparently nothing further that is available for anyone to analyze beyond the two finds that have already seen published work (the strung buttons from Cuatro Cienegas and the Shumla artifacts).
The same is true for the actual Lophophora specimens in herbariums. At UT their entire collection disappeared some years ago along with all of the collection data.
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How sad. That's truly a loss for us all. I can't imagine though that all the burials that are out there have already been excavated. Surely there are a few that remain undiscovered? Also, here's a bit of idle speculation...what if those effigies weren't made from peyote at all? What if they were made from Trichocereus? A peyote shortage all those years ago could have given rise to importers hawking ersatz peyote buttons. I mean really, why would one make peyote effigies from peyote itself? It's not beyond reason to assume there were trade routes from South America up through Texas and points north even 6000 years ago. I'm not a Mesoamerican scholar or anything, so anyone who cares to poke holes in that is more than welcome.  I already asked Alice.
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DMT-Nexus member
Posts: 196 Joined: 15-Jan-2013 Last visit: 09-Feb-2024 Location: paradise
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I would imagine that there are more lurking in the ground someplace. Discovery will be the tricky part.
One fascinating aspect about the Shumla effigies is those were recovered from a residential site rather than a burial.
I'm not inclined to think that trichs ever made it north and then completely disappeared but even there it would seem more likely than not for more alkaloids than just mescaline to be detectable.
I suspect this will remain enigmatic.
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